Bike Tour of Chicago's Lakefront Areas

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Bike Tour of Chicago's Lakefront Areas

By Bobby's Bike, Hike & Food Tours - Chicago

Exceptional

Free cancellation available

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Features

Free cancellation available
3h
Mobile voucher
Instant confirmation

Overview

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognised for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveller, and more! Bobby’s now offers over a dozen specialised tours, but The Lakefront Areas Chicago Bike Tour is what started it all. Join one of Bobby’s expert guides on this 3-hour bicycle tour through Chicago’s beautiful North Side Lakefront areas. See the ever-rising skyscrapers of Streeterville, the deluxe residential mansions of the Gold Coast, the cosy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the world-famous Lakefront Bike Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! This Bicycle Tour of Chicago is kid-friendly and all equipment (bikes, helmets) is included.

Activity location

Museum of Contemporary Art
- 220 E Chicago Ave,
- 60611-2644, Chicago, Illinois, United States

Meeting/Redemption Point

540 N Lake Shore Dr
- 540 North Lake Shore Drive
- 60611, Chicago, Illinois, United States

Check availability

Daytime Chicago Bike Tour

3h
English

Travellers

Language options: English

Starting time: 13:30

Price details

S$75.08 x 1 AdultS$75.08

Total

What's included, what's not

Local tour guide
Bicycle
Helmet
Food and drinks
$10 per person suggested guide service charge. (via Cash, Venmo and PayPal)

Know before you book

Public transport options are available nearby
Specialised infant seats are available
Suitable for all physical fitness levels
This Chicago Bicycle tour is appropriate for all ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided. Child bikes, seats and tagalongs are available.
Storage for larger bags/items available for free
Please note: children must be strong, capable riders and be able to bike for 9 miles
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Chicago Bike Tour operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
Minimum numbers apply for the bike tour of Chicago. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.

Activity itinerary

Museum of Contemporary Art

The Museum of Contemporary Art sits quietly in the Gold Coast, but insiders know it represents Chicago’s bold creative edge. On our Chicago Bike Tour through the iconic Lakefront Areas, you’ll ride past this modern cultural hub tucked between historic mansions and leafy streets. The contrast is powerful—cutting-edge art surrounded by classic Chicago elegance. On this Bicycle Tour in Chicago, our guides share how the MCA helped position the city as a serious player in the global art world, bringing provocative exhibits and boundary-pushing artists to the Midwest. It’s a reminder that Chicago isn’t just about history—it’s about reinvention. Among the most enriching Things to do in Chicago, seeing the Museum of Contemporary Art by bike lets you experience how creativity, architecture, and area charm intersect in one unforgettable Lakefront ride.

Gold Coast

Gold Coast is Chicago elegance at its finest. On our Chicago Bike Tour through the stunning Lakefront Areas, you’ll glide past grand mansions, historic brownstones, and tree-lined streets that whisper stories of old-money ambition and architectural brilliance. Insiders know this area rose from the ashes of the Great Chicago Fire, becoming home to the city’s most influential families. On this immersive Bicycle Tour in Chicago, our guides reveal how industrial titans and cultural leaders shaped this lakeside enclave—while you enjoy lake breezes just streets away. It’s refined, quiet, and rich with history. Among the most captivating Things to do in Chicago, exploring the Gold Coast by bike offers a rare blend of prestige, preservation, and proximity to the water—an unforgettable highlight of our Lakefront adventure.

The Magnificent Mile (Pass by)

The Magnificent Mile is where Chicago puts its confidence on full display. On our Chicago Bike Tour through the iconic Lakefront Areas, you’ll ride past legendary shopfronts, historic hotels, and architectural landmarks that define the city’s commercial heart. Insiders know this stretch of Michigan Avenue was once lined with mansions before evolving into one of the most famous shopping corridors in the world. On this engaging Bicycle Tour in Chicago, our guides share how the Mag Mile became a symbol of Chicago’s resilience and global influence. It’s more than retail—it’s reinvention. Among the essential Things to do in Chicago, seeing The Magnificent Mile by bike gives you perspective beyond the shopfronts, connecting luxury, history, and lakefront energy in one unforgettable ride.

Lincoln Park Zoo

Lincoln Park Zoo is where nature, history, and skyline views come together in the heart of the city. On our Chicago Bike Tour through the beautiful Lakefront Areas, you’ll ride past one of the oldest free zoos in the country, surrounded by green space and just steps from Lake Michigan. Insiders know the zoo dates back to 1868 and reflects Chicago’s long-standing commitment to public access and conservation. On this refreshing Bicycle Tour in Chicago, you’ll hear how Lincoln Park transformed from cemetery grounds after the Great Chicago Fire into one of the city’s most beloved outdoor spaces. Among the most memorable Things to do in Chicago, experiencing Lincoln Park Zoo by bike blends wildlife, lake breezes, and area charm into one vibrant Lakefront adventure.

St Michael Catholic Church in Old Town

St. Michael’s Church in Old Town is one of Chicago’s quiet symbols of resilience. On our Chicago Bike Tour through the historic Lakefront Areas, you’ll ride to this 1852 landmark that famously survived the Great Chicago Fire—one of the few structures left standing when much of the city was reduced to ashes. Insiders know its towering steeple once served as a navigation point for ships on Lake Michigan. On this immersive Bicycle Tour in Chicago, our guides share how Old Town rebuilt around this church, preserving its character while the rest of the city modernised. Among the most meaningful Things to do in Chicago, visiting St. Michael’s by bike connects you to the city’s grit, faith, and rebirth—all woven into a scenic Lakefront ride through Chicago’s most charming areas.

North Avenue Beach

North Avenue Beach is where Chicago’s skyline and lakefront lifestyle collide. On our Chicago Bike Tour through the vibrant Lakefront Areas, you’ll ride along the water with sweeping city views rising dramatically behind the sand. Insiders know this beach offers one of the most photographed skyline angles in the city—especially when you glance south towards city centre. On this refreshing Bicycle Tour in Chicago, you’ll hear how the lakefront was preserved “forever open, clear, and free,” giving Chicagoans unmatched public access to nature in the heart of a major city. It’s active, social, and unmistakably Chicago. Among the most energising Things to do in Chicago, experiencing North Avenue Beach by bike blends fresh air, panoramic views, and area charm into one unforgettable Lakefront adventure.

Lakefront Trail

The Lakefront Bicycle Trail is Chicago’s ultimate outdoor runway. On our Chicago Bike Tour through the breathtaking Lakefront Areas, you’ll cruise this iconic path with Lake Michigan on one side and the skyline towering on the other. Insiders know this 18-mile stretch is where locals run, ride, and reset—especially at sunrise when the city feels wide open and alive. On this immersive Bicycle Tour in Chicago, our guides share how the lakefront was intentionally protected for public use, shaping Chicago’s identity as a city that values access to nature. It’s smooth, scenic, and endlessly photogenic. Among the most unforgettable Things to do in Chicago, riding the Lakefront Trail by bike offers freedom, perspective, and fresh air—an essential highlight of this dynamic Lakefront adventure.

Lake Michigan

Lake Michigan isn’t just a backdrop—it’s Chicago’s defining feature. On our Chicago Bike Tour through the stunning Lakefront Areas, you’ll ride alongside one of the largest freshwater lakes in the world, with open blue water stretching to the horizon. Insiders know that on clear days, it feels more like an ocean than a lake—complete with sailboats, beaches, and that unmistakable Midwest breeze. On this unforgettable Bicycle Tour in Chicago, our guides share how the lake shaped the city’s growth, trade, and identity—and why its shoreline remains “forever open, clear, and free.” Among the most iconic Things to do in Chicago, experiencing Lake Michigan by bike blends skyline views, fresh air, and waterfront energy into one powerful, perspective-shifting Lakefront adventure.

Old Town

Old Town is where Chicago’s past still lives on every block. On our Chicago Bike Tour through the charming Lakefront Areas, you’ll pedal along cobblestone-style streets lined with Victorian-era homes that survived the Great Chicago Fire. Insiders know this area became a haven for artists, comedians, and counterculture thinkers in the 1960s—shaping Chicago’s creative spirit. On this engaging Bicycle Tour in Chicago, our guides reveal how Old Town balances historic preservation with modern energy, from iconic churches to tucked-away gardens. Among the most authentic Things to do in Chicago, exploring Old Town by bike offers character, resilience, and storey—an unforgettable highlight of this scenic Lakefront adventure.

Lincoln Park

Lincoln Park is where elegance, green space, and lakefront living come together. On our Chicago Bike Tour through the picturesque Lakefront Areas, you’ll ride past historic brownstones, shaded streets, and one of the largest urban parks in the country. Insiders know Lincoln Park was once the site of the city cemetery before being transformed into a vibrant public oasis after the Great Chicago Fire. On this immersive Bicycle Tour in Chicago, our guides share how the area blends architectural charm, cultural institutions, and easy access to Lake Michigan. It’s refined yet relaxed—classic Chicago. Among the most rewarding Things to do in Chicago, exploring Lincoln Park by bike offers fresh air, fascinating history, and a true local feel woven into this unforgettable Lakefront adventure.

Streeterville (Pass by)

Streeterville is where ambition meets the lake. On our Chicago Bike Tour through the dynamic Lakefront Areas, you’ll ride through this high-rise enclave built on reclaimed land from the Great Chicago Fire era. Insiders know this area was once a literal sandbar—transformed into one of the city’s most valuable and scenic areas. On this Bicycle Tour in Chicago, you’ll glide past modern towers, tucked-away marinas, and sweeping Lake Michigan views while hearing how Streeterville evolved from shipping chaos to luxury living. It’s a powerful example of Chicago’s constant reinvention. Among the most fascinating Things to do in Chicago, exploring Streeterville by bike offers skyline drama, lake breezes, and a front-row seat to the city’s bold architectural storey—all woven seamlessly into this unforgettable Lakefront ride.

Lincoln Monument Gardens

The Standing Lincoln Statue in Lincoln Park is a quiet but powerful tribute to leadership and legacy. On our Chicago Bike Tour through the scenic Lakefront Areas, you’ll ride to this striking sculpture of Abraham Lincoln—long before he became president—capturing him as a thoughtful, rising statesman. Insiders know this statue predates the more famous Lincoln Memorial in D.C., giving Chicago its own early tribute to the 16th president. On this enriching Bicycle Tour in Chicago, our guides share how Lincoln’s Illinois roots shaped his path—and why this statue reflects the city’s deep connection to his storey. Among the most meaningful Things to do in Chicago, visiting the Standing Lincoln Statue by bike blends history, art, and lakeside beauty into one inspiring Lakefront adventure.

Location

Activity location

Museum of Contemporary Art
- 220 E Chicago Ave,
- 60611-2644, Chicago, Illinois, United States

Meeting/Redemption Point

540 N Lake Shore Dr
- 540 North Lake Shore Drive
- 60611, Chicago, Illinois, United States

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